Spiro-type compound and organic light emitting element comprising same

ABSTRACT

The present specification provides a compound having a spiro structure, and an organic light emitting device including the same.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a national phase entry under 35 U.S.C. §371of International Application No. PCT/KR2016/011418 filed Oct. 12, 2016,published May 4, 2017, which claims priority to Korean PatentApplication No. 10-2015-0150335, filed Oct. 28, 2015, and Korean PatentApplication No. 10-2016-0130746, filed Oct. 10, 2016, all of which areincorporated herein by reference.

TECHNICAL FIELD

The present specification relates to a compound having a spiro structureand an organic light emitting device including the same.

BACKGROUND ART

An organic light emission phenomenon generally refers to a phenomenonconverting electrical energy to light energy using an organic material.An organic light emitting device using an organic light emissionphenomenon normally has a structure including an anode, a cathode, andan organic material layer therebetween. Herein, the organic materiallayer is often formed in a multilayer structure formed with differentmaterials in order to increase efficiency and stability of the organiclight emitting device, and for example, may be formed with a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like. Whena voltage is applied between the two electrodes in such an organic lightemitting device structure, holes and electrons are injected to theorganic material layer from the anode and the cathode, respectively, andwhen the injected holes and electrons meet, excitons are formed, andlight emits when these excitons fall back to the ground state.

Development of new materials for such an organic light emitting devicehas been continuously required.

DISCLOSURE Technical Problem

The present specification describes a compound having a spiro structureand an organic light emitting device including the same.

Technical Solution

One embodiment of the present specification provides a compoundrepresented by the following Chemical Formula 1:

In Chemical Formula 1,

L is a direct bond, a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group,

HAr is a substituted or unsubstituted heterocyclic group; or asubstituted or unsubstituted phosphine oxide group,

R1 to R4 are the same as or different from each other, and eachindependently hydrogen; deuterium; a halogen group; a nitrile group; anitro group; a hydroxyl group; a carbonyl group; an ester group; animide group; a substituted or unsubstituted amine group; a substitutedor unsubstituted silyl group; a substituted or unsubstituted borongroup; a substituted or unsubstituted alkyl group; a substituted orunsubstituted cycloalkyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted aralkylgroup; a substituted or unsubstituted aralkenyl group; a substituted orunsubstituted alkylaryl group; a substituted or unsubstituted alkylaminegroup; a substituted or unsubstituted aralkylamine group; a substitutedor unsubstituted heteroarylamine group; a substituted or unsubstitutedarylamine group; a substituted or unsubstituted arylheteroarylaminegroup; a substituted or unsubstituted arylphosphine group; a substitutedor unsubstituted phosphine oxide group; a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heterocyclic group, or maybond to an adjacent group to form a substituted or unsubstituted ring,

a is an integer of 0 to 7, b is an integer of 0 to 7, c is an integer of0 to 5, d is an integer of 0 to 4, n is an integer of 0 to 10, and whena, b, c, d and n are each 2 or greater, structures in the parenthesesare the same as or different from each other.

Another embodiment of the present specification provides an organiclight emitting device including a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layersinclude the compound of Chemical Formula 1.

Advantageous Effects

Compounds described in the present specification can be used as amaterial of an organic material layer of an organic light emittingdevice. Compounds according to at least one embodiment are capable ofenhancing efficiency, low driving voltage and/or enhancing lifespanproperties in an organic light emitting device. Particularly, compoundsdescribed in the present specification can be used as a material of holeinjection, hole transfer, hole injection and hole transfer, lightemission, electron transfer or electron injection. In addition,compounds described in the present specification can be preferably usedas a material of a light emitting layer, electron transfer or electroninjection. More preferably, when using compounds described in thepresent specification as a material of hole injection, hole transfer andelectron suppression layer, properties of low voltage, high efficiencyand/or long lifespan are exhibited.

DESCRIPTION OF DRAWINGS

FIG. 1 illustrates an organic light emitting device formed with asubstrate (1), an anode (2), a light emitting layer (3) and a cathode(4).

FIG. 2 illustrates an organic light emitting device formed with asubstrate (1), an anode (2), a hole injection layer (5), a hole transferlayer (6), a light emitting layer (3), an electron transfer layer (7)and a cathode (4).

-   -   1: Substrate    -   2: Anode    -   3: Light Emitting Layer    -   4: Cathode    -   5: Hole Injection Layer    -   6: Hole Transfer Layer    -   7: Electron Transfer Layer

MODE FOR DISCLOSURE

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides a compoundrepresented by Chemical Formula 1.

Examples of the substituents are described below, however, thesubstituents are not limited thereto.

In the present specification, the term “substituted or unsubstituted”means being substituted with one or more substituents selected from thegroup consisting of deuterium; a halogen group; a nitrile group; a nitrogroup; a hydroxyl group; a carbonyl group; an ester group; an imidegroup; an amine group; a phosphine oxide group; an alkoxy group; anaryloxy group; an alkylthioxy group; an arylthioxy group; analkylsulfoxy group; an arylsulfoxy group; a silyl group unsubstituted orsubstituted with an alkyl group; a boron group; an alkyl group; acycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; anaralkenyl group; an alkylaryl group; an alkylamine group; anaralkylamine group; a heteroarylamine group; an arylamine group; anarylphosphine group; and a heterocyclic group, or being unsubstituted,or being substituted with a substituent linking two or more substituentsamong the substituents illustrated above, or being unsubstituted. Forexample, “a substituent linking two or more substituents” may include abiphenyl group. In other words, a biphenyl group may be an aryl group,or interpreted as a substituent linking two phenyl groups.

In one embodiment of the present specification, the expression“substituted or unsubstituted” may mean being preferably substitutedwith one or more substituents selected from the group consisting ofdeuterium; a halogen group; a nitrile group; an alkyl group; atrimethylsilyl group; an aryl group; and a heterocyclic group, or beingunsubstituted.

In the present specification, an “adjacent” group may mean a substituentsubstituting an atom directly linked to an atom substituted by thecorresponding substituent, a substituent sterically most closelypositioned to the corresponding substituent, or another substituentsubstituting an atom substituted by the corresponding substituent. Forexample, two substituents substituting ortho positions in a benzenering, and two substituents substituting the same carbon in an aliphaticring may be interpreted as groups “adjacent” to each other.

In the present specification, the number of carbon atoms of the carbonylgroup is not particularly limited, but is preferably from 1 to 40.Specifically, compounds having structures as below may be included,however, the carbonyl group is not limited thereto.

In the present specification, in the ester group, the oxygen of theester group may be substituted with a linear, branched or cyclic alkylgroup having 1 to 25 carbon atoms, or an aryl group having 6 to 25carbon atoms. Specifically, compounds having the following structuralformulae may be included, however, the ester group is not limitedthereto.

In the present specification, the number of carbon atoms of the imidegroup is not particularly limited, but is preferably from 1 to 25.Specifically, compounds having structures as below may be included,however, the imide group is not limited thereto.

In the present specification, the silyl group may be represented by thechemical formula of —SiRR′R″, and R, R′ and R″ may each be hydrogen; asubstituted or unsubstituted alkyl group; or a substituted orunsubstituted aryl group. Specific examples of the silyl group mayinclude a trimethylsilyl group, a triethylsilyl group, at-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group and the like, but are not limited thereto.

In the present specification, the boron group may be represented by thechemical formula of —BRR′, and R and R′ may each be hydrogen; asubstituted or unsubstituted alkyl group; or a substituted orunsubstituted aryl group. Specific examples of the boron group mayinclude a trimethylboron group, a triethylboron group, at-butyldimethylboron group, a triphenylboron group, a phenylboron groupand the like, but are not limited thereto.

In the present specification, examples of the halogen group may includefluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched,and the number of carbon atoms is not particularly limited, but ispreferably from 1 to 40. According to one embodiment, the number ofcarbon atoms of the alkyl group is from 1 to 20. According to anotherembodiment, the number of carbon atoms of the alkyl group is from 1 to10. According to still another embodiment, the number of carbon atoms ofthe alkyl group is from 1 to 6. Specific examples of the alkyl group mayinclude methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl,isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl,n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl,1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl,2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl,2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl,1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl,5-methylhexyl and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear orbranched, and although not particularly limited thereto, the number ofcarbon atoms is preferably from 2 to 40. According to one embodiment,the number of carbon atoms of the alkenyl group is from 2 to 20.According to another embodiment, the number of carbon atoms of thealkenyl group is from 2 to 10. According to still another embodiment,the number of carbon atoms of the alkenyl group is from 2 to 6. Specificexamples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl,2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl,2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl,a stilbenyl group, a styrenyl group and the like, but are not limitedthereto.

In the present specification, the cycloalkyl group is not particularlylimited, but preferably has 3 to 60 carbon atoms, and according to oneembodiment, the number of carbon atoms of the cycloalkyl group is from 3to 30. According to another embodiment, the number of carbon atoms ofthe cycloalkyl group is from 3 to 20. According to still anotherembodiment, the number of carbon atoms of the cycloalkyl group is from 3to 6. Specific examples thereof may include cyclopropyl, cyclobutyl,cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl and the like, but are not limited thereto.

In the present specification, the alkoxy group is not particularlylimited, but preferably has 1 to 40 carbon atoms. According to oneembodiment, the number of carbon atoms of the alkoxy group is from 1 to10. According to another embodiment, the number of carbon atoms of thealkoxy group is from 1 to 6. Specific examples of the alkoxy group mayinclude a methoxy group, an ethoxy group, a propoxy group, anisobutyloxy group, a sec-butyloxy group, a pentyloxy group, aniso-amyloxy group, a hexyloxy group and the like, but are not limitedthereto.

In the present specification, the number of carbon atoms of the aminegroup is not particularly limited, but is preferably from 1 to 30.Specific examples of the amine group may include a methylamine group, adimethylamine group, an ethylamine group, a diethylamine group, aphenylamine group, a naphthylamine group, a biphenylamine group, ananthracenylamine group, a 9-methylanthracenylamine group, adiphenylamine group, a phenylnaphthylamine group, a ditolylamine group,a phenyltolylamine group, a triphenylamine group and the like, but arenot limited thereto.

In the present specification, examples of the arylamine group include asubstituted or unsubstituted monoarylamine group, a substituted orunsubstituted diarylamine group, or a substituted or unsubstitutedtriarylamine group. The aryl group in the arylamine group may be amonocyclic aryl group or a multicyclic aryl group. The arylamine groupincluding two or more aryl groups may include monocyclic aryl groups,multicyclic aryl groups, or both monocyclic aryl groups and multicyclicaryl groups.

Specific examples of the arylamine group may include a phenylaminegroup, a naphthylamine group, a biphenylamine group, an anthracenylaminegroup, a 3-methylphenylamine group, a 4-methylnaphthylamine group, a2-methylbiphenylamine group, a 9-methylanthracenylamine group, adiphenylamine group, a phenylnaphthylamine group, a ditolylamine group,a phenyltolylamine group, carbazole, a triphenylamine group and thelike, but are not limited thereto.

In the present specification, examples of the heteroarylamine groupinclude a substituted or unsubstituted monoheteroarylamine group, asubstituted or unsubstituted diheteroarylamine group, or a substitutedor unsubstituted triheteroarylamine group. The heteroaryl group in theheteroarylamine group may be a monocyclic heterocyclic group or amulticyclic heterocyclic group. The heteroarylamine group including twoor more heterocyclic groups may include monocyclic heterocyclic groups,multicyclic heterocyclic groups, or both monocyclic heterocyclic groupsand multicyclic heterocyclic groups.

In the present specification, the arylheteroarylamine group means anamine group substituted with an aryl group and a heterocyclic group.

In the present specification, examples of the arylphosphine groupinclude a substituted or unsubstituted monoarylphosphine group, asubstituted or unsubstituted diarylphosphine group, or a substituted orunsubstituted triarylphosphine group. The aryl group in thearylphosphine group may be a monocyclic aryl group or a multicyclic arylgroup. The arylphosphine group including two or more aryl groups mayinclude monocyclic aryl groups, multicyclic aryl groups, or bothmonocyclic aryl groups and multicyclic aryl groups.

In the present specification, the aryl group is not particularlylimited, but preferably has 6 to 60 carbon atoms, and may be amonocyclic aryl group or a multicyclic aryl group. According to oneembodiment, the number of carbon atoms of the aryl group is from 6 to30. According to one embodiment, the number of carbon atoms of the arylgroup is from 6 to 20. Examples of the monocyclic aryl group may includea phenyl group, a biphenyl group, a terphenyl group and the like, butare not limited thereto. Examples of the multicyclic aryl group mayinclude a naphthyl group, an anthracenyl group, a phenanthryl group, apyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group,a triphenylene group and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and two of the substituents may bond to each other to form a spirostructure.

When the fluorenyl group is substituted,

and the like may be included. However, the structure is not limitedthereto.

In the present specification, the heterocyclic group is a heterocyclicgroup including one or more of N, O, S, Si and Se as a heteroatom, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 2 to 60. Examples of the heterocyclic group may includea thiophene group, a furan group, a pyrrole group, an imidazole group, atriazole group, an oxazole group, an oxadiazole group, a triazole group,a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group,a triazole group, an acridyl group, a pyridazine group, a pyrazinylgroup, a quinolinyl group, a quinazoline group, a quinoxalinyl group, aphthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group,a pyrazinopyrazinyl group, an isoquinoline group, an indole group, acarbazole group, a benzoxazole group, a benzimidazole group, abenzothiazole group, a benzocarbazole group, a benzothiophene group, adibenzothiophene group, a benzofuranyl group, a phenanthroline group, athiazolyl group, an isoxazolyl group, an oxadiazolyl group, athiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group, aphenothiazinyl group, a dibenzofuranyl group and the like, but are notlimited thereto.

In the present specification, the descriptions on the heterocyclic groupprovided above may be used on the heteroaryl group except that theheteroaryl group is an aromatic group.

In the present specification, the descriptions on the aryl groupprovided above may be used on the aryl group in the aryloxy group, thearylthioxy group, the arylsulfoxy group, the arylphosphine group, thearalkyl group, the aralkylamine group, the aralkenyl group, thealkylaryl group, the arylamine group and the arylheteroarylamine group.

In the present specification, the descriptions on the alkyl groupprovided above may be used on the alkyl group in the alkylthioxy group,the alkylsulfoxy group, the aralkyl group, the aralkylamine group, thealkylaryl group and the alkylamine group.

In the present specification, the descriptions on the heteroaryl groupprovided above may be used on the heteroayl group in the heteroarylgroup, the heteroarylamine group and the arylheteroarylamine group.

In the present specification, the descriptions on the alkenyl groupprovided above may be used on the alkenyl group in the aralkenyl group.

In the present specification, the descriptions on the aryl groupprovided above may be used on the arylene group except that the arylenegroup is divalent.

In the present specification, the descriptions on the heteroaryl groupprovided above may be used on the heteroarylene group except that theheteroarylene group is divalent.

In the present specification, bonding to an adjacent group to form aring means bonding to an adjacent group to form a substituted orunsubstituted aliphatic hydrocarbon ring; a substituted or unsubstitutedaromatic hydrocarbon ring; a substituted or unsubstituted aliphaticheteroring; a substituted or unsubstituted aromatic heteroring; or afused ring thereof.

In the present specification, the aliphatic hydrocarbon ring means aring that is not aromatic and formed only with carbon and hydrogenatoms.

In the present specification, examples of the aromatic hydrocarbon ringmay include benzene, naphthalene, anthracene and the like, but are notlimited thereto.

In the present specification, the aliphatic heteroring means analiphatic ring including one or more of heteroatoms.

In the present specification, the aromatic heteroring means an aromaticring including one or more of heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, thearomatic hydrocarbon ring, the aliphatic heteroring and the aromaticheteroring may be monocyclic or multicyclic.

According to one embodiment of the present specification, ChemicalFormula 1 may be represented by one of the following

Chemical Formulae 2 to 5.

In Chemical Formulae 2 to 5, definitions of substituents are the same asin Chemical Formula 1.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr is a substituted or unsubstituted pyridyl group; asubstituted or unsubstituted pyrimidyl group; a substituted orunsubstituted triazinyl group; a substituted or unsubstituted furangroup; a substituted or unsubstituted thiophene group; a substituted orunsubstituted oxadiazole group; a substituted or unsubstitutedthiadiazole group; a substituted or unsubstituted phenanthroline group;a substituted or unsubstituted quinolinyl group; a substituted orunsubstituted isoquinolinyl group; a substituted or unsubstitutedquinazoline group; a substituted or unsubstituted benzoxazole group; asubstituted or unsubstituted benzothiazole group; a substituted orunsubstituted benzimidazole group; a substituted or unsubstitutedphenoxazine group; a substituted or unsubstituted phenothiazine group; asubstituted or unsubstituted dibenzofuran group; a substituted orunsubstituted dibenzothiophene group; a substituted or unsubstitutedcarbazole group; or a substituted or unsubstituted diarylphosphine oxidegroup.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr may be unsubstituted or substituted with asubstituted or unsubstituted aryl group; a substituted or unsubstitutedheterocyclic group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted heteroarylamine group; or a substituted orunsubstituted arylheteroarylamine group.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr may be unsubstituted or substituted with asubstituted or unsubstituted aryl group or a substituted orunsubstituted heterocyclic group.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr may be unsubstituted or substituted with asubstituted or unsubstituted aryl group.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr may be unsubstituted or substituted with an arylgroup.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, HAr may be unsubstituted or substituted with a phenylgroup or a biphenylyl group.

According to one embodiment of the present application, in ChemicalFormulae 1 to 5, -(L)n-HAr may be represented by the followingstructural formulae.

In the structural formulae,

Ar1 to Ar3 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; a substitutedor unsubstituted heterocyclic group; a substituted or unsubstitutedarylamine group; a substituted or unsubstituted heteroarylamine group;or a substituted or unsubstituted arylheteroarylamine group,

L1 is a direct bond; a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group, and

the structural formulae may be unsubstituted or substituted with one ormore substituents selected from the group consisting of deuterium; ahalogen group; a nitrile group; a nitro group; a hydroxyl group; acarbonyl group; an ester group; an imide group; a substituted orunsubstituted amine group; a phosphine oxide group; an alkoxy group; anaryloxy group; an alkylthioxy group; an arylthioxy group; analkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group;an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; anaralkyl group; an aralkenyl group; an alkylaryl group; an alkylaminegroup; an aralkylamine group; a heteroarylamine group; an arylaminegroup; an arylheteroarylamine group; an arylphosphine group; and aheterocyclic group.

According to one embodiment, the structural formulae illustrated as-(L)n-HAr may be unsubstituted or substituted with a substituted orunsubstituted aryl group; a substituted or unsubstituted heterocyclicgroup; a substituted or unsubstituted arylamine group; a substituted orunsubstituted heteroarylamine group; or a substituted or unsubstitutedarylheteroarylamine group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; or a substituted or unsubstituted monocyclic to pentacyclicarylene group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; or a substituted or unsubstituted monocyclic to tetracyclicarylene group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; or an arylene group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; a substituted or unsubstituted phenylene group; a substituted orunsubstituted divalent biphenyl group; a substituted or unsubstituteddivalent terphenyl group; a substituted or unsubstituted divalentquaterphenyl group; a substituted or unsubstituted divalent naphthylgroup; a substituted or unsubstituted divalent anthracenyl group; asubstituted or unsubstituted divalent fluorenyl group; a substituted orunsubstituted divalent phenanthryl group; a substituted or unsubstituteddivalent pyrenyl group; or a substituted or unsubstituted divalentchrysenyl group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; a phenylene group; a divalent biphenyl group; a divalent terphenylgroup; a divalent quaterphenyl group; a divalent naphthyl group; adivalent anthracenyl group; a divalent fluorenyl group; a divalentphenanthryl group; a divalent pyrenyl group; or a divalent chrysenylgroup.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently asubstituted or unsubstituted heteroarylene group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently asubstituted or unsubstituted heteroarylene group including O, N or S.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently aheteroarylene group including O, N or S.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond or any one selected from among the following structural formulae.

In the structural formulae,

A1 and A2 are the same as or different from each other, and eachindependently hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group, or may bond to each other to form asubstituted or unsubstituted ring, and

the structures may be unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; a substituted or unsubstitutedamine group; a phosphine oxide group; an alkoxy group; an aryloxy group;an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; anarylsulfoxy group; a silyl group; a boron group; an alkyl group; acycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; anaralkenyl group; an alkylaryl group; an alkylamine group; anaralkylamine group; a heteroarylamine group; an arylamine group; anarylphosphine group; and a heterocyclic group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond or any one selected from among the following structural formulae.

In the structural formulae,

A1 and A2 are the same as or different from each other, and eachindependently hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group, or may bond to each other to form asubstituted or unsubstituted ring, and

the structures may be unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; a substituted or unsubstitutedamine group; a phosphine oxide group; an alkoxy group; an aryloxy group;an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; anarylsulfoxy group; a silyl group; a boron group; an alkyl group; acycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; anaralkenyl group; an alkylaryl group; an alkylamine group; anaralkylamine group; a heteroarylamine group; an arylamine group; anarylphosphine group; and a heterocyclic group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; or any one selected from among the following structural formulae.

In the structural formulae,

A1 and A2 are the same as or different from each other, and eachindependently hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heterocyclic group, or may bond to each other to form asubstituted or unsubstituted ring, and

the structures may be unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; a substituted or unsubstitutedamine group; a phosphine oxide group; an alkoxy group; an aryloxy group;an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; anarylsulfoxy group; a silyl group; a boron group; an alkyl group; acycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; anaralkenyl group; an alkylaryl group; an alkylamine group; anaralkylamine group; a heteroarylamine group; an arylamine group; anarylphosphine group; and a heterocyclic group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; a phenylene group; a biphenylylene group; or a fluorenylene group.

According to one embodiment of the present disclosure, L and L1 are thesame as or different from each other, and each independently a directbond; or a phenylene group.

According to one embodiment of the present disclosure, in the structuralformulae described above, Ar1 to Ar3 are the same as or different fromeach other, and each independently a substituted or unsubstituted arylgroup; or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, in the structuralformulae described above, Ar1 to Ar3 are the same as or different fromeach other, and each independently a substituted or unsubstituted arylgroup.

According to one embodiment of the present disclosure, in the structuralformulae described above, Ar1 to Ar3 are the same as or different fromeach other, and each independently a phenyl group; a biphenylyl group;or a naphthyl group.

According to one embodiment of the present disclosure, the compound ofChemical Formula 1 may be any one selected from among the followingcompounds.

The compound represented by Chemical Formula 1 may be prepared based onpreparation examples described below.

According to one embodiment, the compound represented by ChemicalFormula 1 may be prepared through steps of the following ReactionFormulae 1-1 and 1-2.

In the reaction formulae, definitions of L1 and HAr are the same asthose described above.

Those skilled in the art may modify the reaction conditions, reagentsand starting materials described in the reaction formulae describedabove using technologies known in the art, and may further introducesubstituents as necessary.

In addition, the present specification provides an organic lightemitting device including the compound represented by Chemical Formula1.

One embodiment of the present specification provides an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; and one or more organic material layersprovided between the first electrode and the second electrode, whereinone or more layers of the organic material layers include the compoundof Chemical Formula 1.

The organic material layer of the organic light emitting device of thepresent specification may be formed in a single layer structure, but maybe formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice of the present disclosure may have a structure including a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like as theorganic material layer. However, the structure of the organic lightemitting device is not limited thereto, and may include less numbers oforganic material layers.

In one embodiment of the present specification, the organic materiallayer includes a hole injection layer, a hole transfer layer or a layercarrying out hole injection and transfer at the same time, and the holeinjection layer, the hole transfer layer, or the layer carrying out holeinjection and transfer at the same time includes the compound ofChemical Formula 1.

In another embodiment, the organic material layer includes a lightemitting layer, and the light emitting layer includes the compound ofChemical Formula 1. According to one embodiment, the compound ofChemical Formula 1 performs a role of a host of the light emittinglayer, and in this case, the light emitting layer may further include adopant. As the dopant, those known in the art may be used, and forexample, phosphorescent dopants, specifically, iridium-based dopants maybe used therewith. As the iridium-based dopant, Ir(ppy)₃,[(piq)₂Ir(acac)] and the like may be used.

In one embodiment of the present specification, the organic materiallayer includes an electron suppression layer, and the electronsuppression layer includes the compound of Chemical Formula 1.

In one embodiment of the present specification, the electron transferlayer, the electron injection layer, or the layer carrying out electrontransfer and electron injection at the same time includes the compoundof Chemical Formula 1.

In another embodiment, the organic material layer includes a lightemitting layer and an electron transfer layer, and the electron transferlayer includes the compound of Chemical Formula 1.

The electron transfer layer may further include an n-type dopant asnecessary. As the n-type dopant, those known in the art may be used, andfor example, Li complexes, specifically, LiQ, may be used.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, and the light emittinglayer includes a compound represented by the following Chemical Formula1-A.

In Chemical Formula 1-A,

z1 is an integer of 1 or greater, and when z1 is 2 or greater,structures in the parentheses are the same as or different from eachother,

Ar100 is a substituted or unsubstituted monovalent or higherbenzofluorene group; a substituted or unsubstituted monovalent or higherfluoranthene group; a substituted or unsubstituted monovalent or higherpyrene group; or a substituted or unsubstituted monovalent or higherchrysene group,

L100 is a direct bond; a substituted or unsubstituted arylene group; ora substituted or unsubstituted heteroarylene group,

R100 and R101 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; a substitutedor unsubstituted alkyl group; a substituted or unsubstituted silylgroup; a substituted or unsubstituted arylalkyl group; or a substitutedor unsubstituted heterocyclic group, or may bond to each other to form asubstituted or unsubstituted ring.

According to one embodiment of the present specification, the lightemitting layer includes the compound represented by Chemical Formula 1-Aas a dopant of the light emitting layer.

According to one embodiment of the present specification, L100 is adirect bond.

According to one embodiment of the present specification, z1 is 2.

According to one embodiment of the present specification, Ar100 is adivalent pyrene group unsubstituted or substituted with deuterium, amethyl group, an ethyl group, an iso-propyl group or a tert-butyl group;or a divalent chrysene group unsubstituted or substituted withdeuterium, a methyl group, an ethyl group, an iso-propyl group or atert-butyl group.

According to one embodiment of the present specification, Ar100 is adivalent pyrene group unsubstituted or substituted with deuterium, amethyl group, an ethyl group, an iso-propyl group or a tert-butyl group.

According to one embodiment of the present specification, Ar100 is adivalent pyrene group.

According to one embodiment of the present specification, R100 and R101are the same as or different from each other, and each independently asubstituted or unsubstituted aryl group having 6 to 60 carbon atoms; ora substituted or unsubstituted heterocyclic group having 2 to 60 carbonatoms.

According to one embodiment of the present specification, R100 and R101are the same as or different from each other, and each independently anaryl group having 6 to 60 carbon atoms unsubstituted or substituted withdeuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilylgroup or an alkylgermanium group; or a heterocyclic group having 2 to 60carbon atoms unsubstituted or substituted with deuterium, an alkylgroup, a nitrile group, an aryl group, an alkylsilyl group or analkylgermanium group.

According to one embodiment of the present specification, R100 and R101are the same as or different from each other, and each independently anaryl group having 6 to 60 carbon atoms unsubstituted or substituted withdeuterium, a methyl group, an ethyl group, an iso-propyl group, atert-butyl group, a nitrile group, a phenyl group, a trimethylsilylgroup or a trimethylgermanium group; or a heterocyclic group having 2 to60 carbon atoms unsubstituted or substituted with deuterium, a methylgroup, an ethyl group, an iso-propyl group, a tert-butyl group, anitrile group, a phenyl group, a trimethylsilyl group or atrimethylgermanium group.

According to one embodiment of the present specification, R100 and R101are the same as or different from each other, and each independently aphenyl group unsubstituted or substituted with deuterium, a methylgroup, an ethyl group, an iso-propyl group, a tert-butyl group, anitrile group, a phenyl group, a trimethylsilyl group or atrimethylgermanium group; a biphenyl group unsubstituted or substitutedwith deuterium, a methyl group, an ethyl group, an iso-propyl group, atert-butyl group, a nitrile group, a phenyl group, a trimethylsilylgroup or a trimethylgermanium group; a terphenyl group unsubstituted orsubstituted with deuterium, a methyl group, an ethyl group, aniso-propyl group, a tert-butyl group, a nitrile group, a phenyl group, atrimethylsilyl group or a trimethylgermanium group; or a dibenzofurangroup unsubstituted or substituted with deuterium, a methyl group, anethyl group, an iso-propyl group, a tert-butyl group, a nitrile group, aphenyl group, a trimethylsilyl group or a trimethylgermanium group.

According to one embodiment of the present specification, R100 and R101are the same as or different from each other, and each independently aphenyl group unsubstituted or substituted with a trimethylgermaniumgroup.

According to one embodiment of the present specification, R100 is aphenyl group.

According to one embodiment of the present specification, R101 is aphenyl group substituted with a trimethylgermanium group.

According to one embodiment of the present specification, ChemicalFormula 1-A may be selected from among the following compounds.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, and the light emittinglayer includes a compound represented by the following Chemical Formula1-B.

In Chemical Formula 1-B,

Ar101 and Ar102 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group,

L101 and L102 are the same as or different from each other, and eachindependently a direct bond; a substituted or unsubstituted arylenegroup; or a substituted or unsubstituted heteroarylene group,

R102 is hydrogen; deuterium; a halogen group; a nitrile group; a nitrogroup; a hydroxyl group; a carbonyl group; an ester group; an imidegroup; a substituted or unsubstituted amine group; a substituted orunsubstituted silyl group; a substituted or unsubstituted boron group; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedcycloalkyl group; a substituted or unsubstituted alkoxy group; asubstituted or unsubstituted aryloxy group; a substituted orunsubstituted alkylthioxy group; a substituted or unsubstitutedarylthioxy group; a substituted or unsubstituted alkylsulfoxy group; asubstituted or unsubstituted arylsulfoxy group; a substituted orunsubstituted alkenyl group; a substituted or unsubstituted aralkylgroup; a substituted or unsubstituted aralkenyl group; a substituted orunsubstituted alkylaryl group; a substituted or unsubstituted alkylaminegroup; a substituted or unsubstituted aralkylamine group; a substitutedor unsubstituted heteroarylamine group; a substituted or unsubstitutedarylamine group; a substituted or unsubstituted arylheteroarylaminegroup; a substituted or unsubstituted arylphosphine group; a substitutedor unsubstituted phosphine oxide group; a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heterocyclic group,

z2 and z3 are the same as or different from each other and eachindependently an integer of 1 or 2, z4 is an integer of 0 to 8, and whenz2 to z4 are 2 or greater, substituents in the parentheses are the sameas or different from each other,

m is an integer of 1 or greater, and when m is an integer of 2 orgreater, substituents in the parentheses are the same as or differentfrom each other.

According to one embodiment of the present specification, the lightemitting layer includes the compound represented by Chemical Formula 1-Bas a host of the light emitting layer.

According to one embodiment of the present specification, Ar101 andAr102 are the same as or different from each other, and eachindependently a substituted or unsubstituted aryl group having 6 to 60carbon atoms; or a substituted or unsubstituted heterocyclic grouphaving 2 to 60 carbon atoms.

According to one embodiment of the present specification, Ar101 andAr102 are the same as or different from each other, and eachindependently an aryl group having 6 to 60 carbon atoms unsubstituted orsubstituted with an alkyl group, an aryl group or a heterocyclic group;or a heterocyclic group having 2 to 60 carbon atoms unsubstituted orsubstituted with an alkyl group, an aryl group or a heterocyclic group.

According to one embodiment of the present specification, Ar101 andAr102 are the same as or different from each other, and eachindependently a phenyl group unsubstituted or substituted with an arylgroup or a heterocyclic group; a biphenyl group unsubstituted orsubstituted with an aryl group or a heterocyclic group; a terphenylgroup unsubstituted or substituted with an aryl group or a heterocyclicgroup; a naphthyl group unsubstituted or substituted with an aryl groupor a heterocyclic group; a fluorene group unsubstituted or substitutedwith an alkyl group, an aryl group or a heterocyclic group; aphenanthrene group unsubstituted or substituted with an aryl group or aheterocyclic group; or a triphenylene group unsubstituted or substitutedwith an aryl group or a heterocyclic group.

According to one embodiment of the present specification, Ar101 andAr102 are the same as or different from each other, and eachindependently a phenyl group; a biphenyl group; a terphenyl group; anaphthyl group; a fluorene group unsubstituted or substituted with amethyl group or a phenyl group; a phenanthrene group; or a triphenylenegroup.

According to one embodiment of the present specification, Ar101 is a2-naphthyl group.

According to one embodiment of the present specification, Ar102 is aphenyl group.

According to one embodiment of the present specification, L101 and L102are the same as or different from each other, and each independently adirect bond; a phenylene group; or a naphthylene group.

According to one embodiment of the present specification, L101 is aphenylene group.

According to one embodiment of the present specification, L102 is adirect bond.

According to one embodiment of the present specification, z2 is 1.

According to one embodiment of the present specification, z3 is 1.

According to one embodiment of the present specification, R102 ishydrogen.

According to one embodiment of the present specification, m is 1.

According to one embodiment of the present specification, m is 2.

According to one embodiment of the present specification, ChemicalFormula 1-B may be selected from among the following compounds.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, the light emitting layerincludes the compound represented by Chemical Formula 1-A as a dopant ofthe light emitting layer, and includes the compound represented byChemical Formula 1-B as a host of the light emitting layer.

One embodiment of the present specification provides an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; a light emitting layer provided betweenthe first electrode and the second electrode; and two or more organicmaterial layers provided between the light emitting layer and the firstelectrode, or between the light emitting layer and the second electrode,wherein at least one of the two or more organic material layers includesthe compound having a spiro structure. In one embodiment, as the two ormore organic material layers, two or more may be selected from the groupconsisting of an electron transfer layer, an electron injection layer, alayer carrying out electron transfer and electron injection at the sametime, and a hole blocking layer.

In one embodiment of the present specification, the organic materiallayer includes two or more electron transfer layers, and at least one ofthe two or more electron transfer layers includes the compound having aspiro structure. Specifically, in one embodiment of the presentspecification, the compound having a spiro structure the compound may beincluded in one of the two or more electron transfer layers, or may beincluded in each of the two or more electron transfer layers.

In addition, in one embodiment of the present specification, when thecompound having a spiro structure is included in each of the two or moreelectron transfer layers, materials other than the compound having aspiro structure may be the same as or different from each other.

In another embodiment, the organic light emitting device may be anorganic light emitting device having a structure of consecutivelylaminating an anode, one or more organic material layers and a cathodeon a substrate (normal type).

In another embodiment, the organic light emitting device may be anorganic light emitting device having a reverse structure ofconsecutively laminating a cathode, one or more organic material layersand an anode on a substrate (inverted type).

For example, structures of an organic light emitting device according toone embodiment of the present specification are illustrated in FIG. 1and FIG. 2.

FIG. 1 illustrates an organic light emitting device formed with asubstrate (1), an anode (2), a light emitting layer (3) and a cathode(4). In such a structure, the compound may be included in the lightemitting layer.

FIG. 2 illustrates an organic light emitting device formed with asubstrate (1), an anode (2), a hole injection layer (5), a hole transferlayer (6), a light emitting layer (3), an electron transfer layer (7)and a cathode (4). In such a structure, the compound may be included inone or more layers of the hole injection layer, the hole transfer layer,the light emitting layer and the electron transfer layer.

The organic light emitting device of the present specification may bemanufactured using materials and methods known in the art, except thatone or more layers of the organic material layers include the compoundof the present specification, that is, the compound of Chemical Formula1.

When the organic light emitting device includes a plurality of organicmaterial layers, the organic material layers may be formed withmaterials the same as or different from each other.

The organic light emitting device of the present specification may bemanufactured using materials and methods known in the art, except thatone or more layers of the organic material layers include the compoundof Chemical Formula 1, that is, the compound represented by ChemicalFormula 1.

For example, the organic light emitting device of the presentspecification may be manufactured by consecutively laminating a firstelectrode, an organic material layer and a second electrode on asubstrate. Herein, the organic light emitting device may be manufacturedby forming an anode on a substrate by depositing a metal, a metal oxidehaving conductivity, or an alloy thereof using a physical vapordeposition (PVD) method such as sputtering or e-beam evaporation, andforming an organic material layer including a hole injection layer, ahole transfer layer, a light emitting layer and an electron transferlayer thereon, and then depositing a material capable of being used as acathode thereon. In addition to such a method, the organic lightemitting device may also be manufactured by consecutively depositing acathode material, an organic material layer and an anode material on asubstrate.

In addition, the compound of Chemical Formula 1 may be formed into theorganic material layer using a solution coating method as well as avacuum deposition method when manufacturing the organic light emittingdevice. Herein, the solution coating method means spin coating, dipcoating, doctor blading, inkjet printing, screen printing, a spraymethod, roll coating and the like, but is not limited thereto.

In addition to such a method, the organic light emitting device may bemanufactured by consecutively depositing a cathode material, an organicmaterial layer and an anode material on a substrate (InternationalPatent Application Laid-Open Publication No. 2003/012890). However, themanufacturing method is not limited thereto.

In one embodiment of the present specification, the first electrode isan anode, and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode, and the secondelectrode is an anode.

As the anode material, materials having large work function are normallypreferable so that hole injection to an organic material layer issmooth. Specific examples of the anode material capable of being used inthe present disclosure include metals such as vanadium, chromium,copper, zinc and gold, or alloys thereof; metal oxides such as zincoxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO);combinations of metals and oxides such as ZnO:Al or SnO₂:Sb; conductivepolymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole andpolyaniline, but are not limited thereto.

As the cathode material, materials having small work function arenormally preferable so that electron injection to an organic materiallayer is smooth. Specific examples of the cathode material capable ofbeing used in the present disclosure include metals such as magnesium,calcium, sodium, potassium, titanium, indium, yttrium, lithium,gadolinium, aluminum, silver, tin and lead, or alloys thereof;multilayer structure materials such as LiF/Al or LiO₂/Al, and the like,but are not limited thereto.

The hole injection layer is a layer that injects holes from anelectrode, and the hole injection material is preferably a compound thathas an ability to transfer holes, therefore, has a hole injection effectin an anode, has an excellent hole injection effect for a light emittinglayer or a light emitting material, prevents excitons generated in thelight emitting layer from moving to an electron injection layer or anelectron injection material, and in addition, has an excellent thin filmforming ability. The highest occupied molecular orbital (HOMO) of thehole injection material is preferably in between the work function of ananode material and the HOMO of surrounding organic material layers.Specific examples of the hole injection material include metalporphyrins, oligothiophene, arylamine-based organic materials,hexanitrile hexaazatriphenylene-based organic materials,quinacridone-based organic materials, perylene-based organic materials,anthraquinone, and polyaniline- and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

The hole transfer layer is a layer that receives holes from a holeinjection layer and transfers the holes to a light emitting layer, andas the hole transfer material, materials capable of receiving holes froman anode or a hole injection layer, moving the holes to a light emittinglayer, and having high mobility for the holes are suitable. Specificexamples thereof include arylamine-based organic materials, conductivepolymers, block copolymers having conjugated parts and non-conjugatedparts together, and the like, but are not limited thereto.

The light emitting material is a material capable of emitting light in avisible light region by receiving holes and electrons from a holetransfer layer and an electron transfer layer, respectively, and bindingthe holes and the electrons, and is preferably a material havingfavorable quantum efficiency for fluorescence or phosphorescence.Specific examples thereof include 8-hydroxyquinoline aluminum complexes(Alq₃); carbazole-based compounds; dimerized styryl compounds; BAlq;10-hydroxybenzo quinoline-metal compounds; benzoxazole-, benzthiazole-and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-basedpolymers; spiro compounds; polyfluorene, rubrene, and the like, but arenot limited thereto.

The light emitting layer may include a host material and a dopantmaterial. The host material includes fused aromatic ring derivatives,heteroring-containing compounds or the like. Specifically, the fusedaromatic ring derivative includes anthracene derivatives, pyrenederivatives, naphthalene derivatives, pentacene derivatives,phenanthrene compounds, fluoranthene compounds and the like, and theheteroring-containing compound includes carbazole derivatives,dibenzofuran derivatives, ladder-type furan compounds, pyrimidinederivatives and the like, but the material is not limited thereto.

The dopant material includes aromatic amine derivatives, styrylaminecompounds, boron complexes, fluoranthene compounds, metal complexes andthe like. Specifically, the aromatic amine derivative is a fusedaromatic ring derivative having a substituted or unsubstituted arylaminegroup and includes arylamine group-including pyrene, anthracene,chrysene, peryflanthene and the like, and the styrylamine compound is acompound in which substituted or unsubstituted arylamine is substitutedwith at least one arylvinyl group, and one, two or more substituentsselected from the group consisting of an aryl group, a silyl group, analkyl group, a cycloalkyl group and an arylamine group are substitutedor unsubstituted. Specifically, styrylamine, styryldiamine,styryltriamine, styryltetramine or the like is included, but thestyrylamine compound is not limited thereto. In addition, the metalcomplex includes iridium complexes, platinum complexes or the like, butis not limited thereto.

The electron transfer layer is a layer that receives electrons from anelectron injection layer and transfers the electrons to a light emittinglayer, and as the electron transfer material, materials capable offavorably receiving electrons from a cathode, moving the electrons to alight emitting layer, and having high mobility for the electrons aresuitable. Specific examples thereof include Al complexes of8-hydroxyquinoline; complexes including Alq₃; organic radical compounds;hydroxyflavon-metal complexes, and the like, but are not limitedthereto. The electron transfer layer may be used together with anydesired cathode material as used in the art. Particularly, examples ofthe suitable cathode material include common materials that have smallwork function, and in which an aluminum layer or a silver layer follows.Specifically, the cathode material includes cesium, barium, calcium,ytterbium and samarium, and in each case, an aluminum layer or a silverlayer follows.

The electron injection layer is a layer that injects electrons from anelectrode, and the electron injection material is preferably a compoundthat has an ability to transfer electrons, has an electron injectioneffect from a cathode, has an excellent electron injection effect for alight emitting layer or a light emitting material, prevents excitonsgenerated in the light emitting layer from moving to a hole injectionlayer, and in addition, has an excellent thin film forming ability.Specific examples thereof include fluorenone, anthraquinodimethane,diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole,imidazole, perylene tetracarboxylic acid, fluorenylidene methane,anthrone or the like, and derivatives thereof, metal complex compounds,nitrogen-containing 5-membered ring derivatives, and the like, but arenot limited thereto.

The metal complex compound includes 8-hydroxyquinolinato lithium,bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)berylium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(0-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but is not limited thereto.

The organic light emitting device according to the present specificationmay be a top-emission type, a bottom-emission type or a dual-emissiontype depending on the materials used.

Preparation of the compound represented by Chemical Formula 1, andmanufacture of the organic light emitting device including the same willbe specifically described with reference to the following examples.However, the following examples are for illustrative purposes only, andthe scope of the present specification is not limited thereto.

Preparation Example 1

Compound Synthesis of the Following Compound 1

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (5.31 g, 18.98 mmol) in 230 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 5 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 270 ml of ethylacetate to prepare Compound 1 (10.36 g, 88%).

MS [M+H]⁺=712

Preparation Example 2

Compound Synthesis of the Following Compound 2

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-chloro-4,6-diphenylpyrimidine (5.31 g, 18.98 mmol) in 250 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 4 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 230 ml of ethylacetate to prepare Compound 2 (9.78 g, 83%).

MS[M+H]⁺=711

Preparation Example 3

Compound Synthesis of the Following Compound 3

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and4-chloro-2,6-diphenylpyrimidine (5.31 g, 18.98 mmol) in 260 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 3 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 240 ml of ethylacetate to prepare Compound 3 (8.65 g, 74%).

MS[M+H]⁺=711

Preparation Example 4

Compound Synthesis of the Following Compound 4

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-chloro-4,6-diphenylpyridine (3.1 g, 18.98 mmol) in 280 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 2 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 280 ml of ethylacetate to prepare Compound 4 (7.74 g, 66%).

MS[M+H]⁺=710

Preparation Example 5

Compound Synthesis of the Following Compound 5

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (6.51 g, 18.98 mmol) in250 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 5 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 300 ml of ethylacetate to prepare Compound 5 (10.36 g, 88%).

MS[M+H]⁺=788

Preparation Example 6

Compound Synthesis of the Following Compound 6

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-chloro-4-phenylquinazoline (4.57 g, 18.98 mmol) in 250 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 6 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 230 ml of ethylacetate to prepare Compound 6 (9.95 g, 74%).

MS[M+H]⁺=685

Preparation Example 7

Compound Synthesis of the Following Compound 7

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and3-bromo-9-phenyl-9H-carbazole (6.09 g, 18.98 mmol) in 250 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 6 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 230 ml of ethylacetate to prepare Compound 7 (12.05 g, 85%).

MS[M+H]⁺=722

Preparation Example 8

Compound Synthesis of the Following Compound 8

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and(4-bromophenyl)diphenylphosphine oxide (7.71 g, 18.98 mmol) in 250 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 4 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 310 ml of ethylacetate to prepare Compound 8 (13.97 g, 94%).

MS[M+H]⁺=757

Preparation Example 9

Compound Synthesis of the Following Compound 9

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole (7.71 g, 18.98 mmol) in250 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 4 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 310 ml of ethylacetate to prepare Compound 9 (12.24 g, 83%).

MS[M+H]⁺=749

Preparation Example 10

Compound Synthesis of the Following Compound 10

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-bromodibenzo[b,d]furan (4.69 g, 18.98 mmol) in 290 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 3 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 230 ml of ethylacetate to prepare Compound 10 (7.53 g, 59%).

MS[M+H]⁺=647

Preparation Example 11

Compound Synthesis of the Following Compound 11

After completely dissolving Compound B-1 (10.0 g, 16.50 mmol) and2-bromodibenzo[b,d]thiophene (4.99 g, 18.98 mmol) in 290 ml oftetrahydrofuran in a 500 ml round bottom flask under nitrogenatmosphere, an aqueous 2 M potassium carbonate solution (125 ml) andthen tetrakis-(triphenylphosphine)palladium (0.19 g, 0.17 mmol) wereadded thereto, and the result was heated and stirred for 3 hours. Thetemperature was lowered to room temperature, the water layer wasremoved, and the result was dried with anhydrous magnesium sulfate,vacuum concentrated, and then recrystallized with 230 ml of ethylacetate to prepare Compound 11 (7.53 g, 59%).

MS[M+H]⁺=663

<Preparation Example 12> to <Preparation Example 22>

Compounds 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 and 22 were prepared inthe same manner as in Preparation Examples 1 to 11 except that CompoundC-1 was used as the staring material instead of Compound B-1.

TABLE 1 Compound MS [M + H]⁺ 12 712 13 711 14 711 15 710 16 788 17 68518 722 19 757 20 749 21 647 22 663

<Preparation Example 23> to <Preparation Example 33>

Compounds 23, 24, 25, 26, 27, 28, 29, 30, 31, 32 and 33 were prepared inthe same manner as in Preparation Examples 1 to 11 except that CompoundD-1 was used as the staring material instead of Compound B-1.

TABLE 2 Compound MS [M + H]⁺ 23 712 24 711 25 711 26 710 27 788 28 68529 722 30 757 31 749 32 647 33 663

<Preparation Example 34> to <Preparation Example 44>

Compounds 34, 35, 36, 37, 38, 39, 40, 41, 42, 43 and 44 were prepared inthe same manner as in Preparation Examples 1 to 11 except that CompoundA-1 was used as the staring material instead of Compound B-1.

TABLE 3 Compound MS [M + H]⁺ 34 712 35 711 36 711 37 710 38 788 39 68540 722 41 757 42 749 43 647 44 663

Example 1

The compounds synthesized in the synthesis examples were high-puritysublimation purified using commonly known methods, and then a greenorganic light emitting device was manufactured using a method as below.

A glass substrate on which indium tin oxide (ITO) was coated as a thinfilm to a thickness of 1,000 Å was placed in detergent-dissolveddistilled water and ultrasonic cleaned. Herein, a product of Fischer Co.was used as the detergent, and as the distilled water, distilled waterfiltered twice with a filter manufactured by Millipore Co. was used.After the ITO was cleaned for 30 minutes, ultrasonic cleaning wasrepeated twice using distilled water for 10 minutes. After the cleaningwith distilled water was finished, the substrate was ultrasonic cleanedwith solvents of isopropyl alcohol, acetone and methanol, then dried,and then transferred to a plasma cleaner. In addition, the substrate wascleaned for 5 minutes using oxygen plasma, and then transferred to avacuum depositor.

An organic light emitting device was manufactured by forming a lightemitting element in the order of m-MTDATA (60 nm)/TCTA (80 nm)/CBP+10%Ir(ppy)₃ (300 nm)/BCP (10 nm)/Alq₃ (30 nm)/LiF (1 nm)/Al (200 nm) on thetransparent ITO electrode prepared as above using CBP as a host.

Structures of the m-MTDATA, the TCTA, the Ir(ppy)₃, the CBP and the BCPare as follows.

Example 1-1

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 1 was used instead of CBP.

Example 1-2

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 2 was used instead of CBP.

Example 1-3

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 3 was used instead of CBP.

Example 1-4

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 4 was used instead of CBP.

Example 1-5

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 5 was used instead of CBP.

Example 1-6

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 12 was used instead of CBP.

Example 1-7

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 13 was used instead of CBP.

Example 1-8

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 14 was used instead of CBP.

Example 1-9

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 15 was used instead of CBP.

Example 1-10

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 16 was used instead of CBP.

Example 1-11

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 23 was used instead of CBP.

Example 1-12

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 24 was used instead of CBP.

Example 1-13

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 25 was used instead of CBP.

Example 1-14

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 26 was used instead of CBP.

Example 1-15

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 27 was used instead of CBP.

Example 1-16

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 34 was used instead of CBP.

Example 1-17

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 35 was used instead of CBP.

Example 1-18

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 36 was used instead of CBP.

Example 1-19

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 37 was used instead of CBP.

Example 1-20

An organic light emitting device was manufactured in the same manner asin Example 1 except that Compound 38 was used instead of CBP.

When a current was applied to the organic light emitting devicesmanufactured in Example 1, and Examples 1-1 to 1-20, results of Table 4were obtained.

TABLE 4 EL Compound Voltage Efficiency Peak (Host) (V@10 mA/cm²)(cd/A@10 mA/cm²) (nm) Example 1 CBP 7.45 38.12 516 Example Compound 16.30 43.53 517 1-1 Example Compound 2 6.32 43.14 517 1-2 ExampleCompound 3 6.31 43.32 517 1-3 Example Compound 4 6.22 44.45 518 1-4Example Compound 5 6.30 43.31 517 1-5 Example Compound 6.23 44.63 5171-6 12 Example Compound 6.31 43.02 516 1-7 13 Example Compound 6.3243.24 513 1-8 14 Example Compound 6.22 44.38 516 1-9 15 Example Compound6.31 43.82 516 1-10 16 Example Compound 6.32 43.50 517 1-11 23 ExampleCompound 6.31 43.16 516 1-12 24 Example Compound 6.32 43.23 516 1-13 25Example Compound 6.26 44.44 516 1-14 26 Example Compound 6.31 43.62 5161-15 27 Example Compound 6.29 44.75 516 1-16 34 Example Compound 6.3843.91 516 1-17 35 Example Compound 6.23 44.83 517 1-18 36 ExampleCompound 6.24 44.42 516 1-19 37 Example Compound 6.27 44.54 517 1-20 38

From the test results, it was identified that the green organic lightemitting devices of Examples 1-1 to 1-20 using the compounds accordingto the present disclosure as a host material of the light emitting layerexhibited superior performance in terms of current efficiency anddriving voltage compared to the green organic light emitting device ofExample 1 using existing CBP. Particularly, it was seen that thecompounds having triazine, pyrimidine or pyridine as a substituent weresuitable for a green organic light emitting device.

Example 2

The compounds synthesized in the preparation examples were high-puritysublimation purified using commonly known methods, and then a redorganic light emitting device was manufactured using a method as below.

An ITO glass was patterned so that a light emitting area became a 2 mm×2mm size, and then cleaned. After installing the substrate in a vacuumchamber, the base pressure was set at 1×10⁶ torr, and as organicmaterials on the ITO, a DNTPD layer (700 Å) and an α-NPB layer (300 Å)were formed, and a light emitting layer was prepared by using CBP as ahost (90 wt %) and vacuum depositing (300 Å) the following(piq)₂Ir(acac) (10 wt %) as a dopant. Subsequently, an Alq₃ layer (350Å), a LiF layer (5 Å) and an Al layer (1,000 Å) were formed in thisorder, and properties of the device were measured at 0.4 mA.

Structures of the DNTPD, the α-NPB, the (piq)₂Ir(acac) and the Alq₃ areas follows.

<Example 2-1> to <Example 2-4>

Organic light emitting devices were manufactured in the same manner asin Example 2 except that Compounds 7, 18, 29 and 40 prepared in thepreparation examples described above were respectively used instead ofCBP.

For the organic light emitting devices manufactured according toExamples 2-1 to 2-4, and Example 2, a voltage, current density,luminance, a color coordinate and a lifespan were measured, and theresults are shown in the following Table 5. T95 means time taken for theluminance decreasing to 95% of its initial luminance (5000 nit).

TABLE 5 Compound Luminance CIEx CIEy T95 Category (Host) Dopant Voltage(V) (cd/m²) (cd/m²) (hr) Example Compound 7 [(piq)₂Ir(acac)] 4.3 17600.670 0.329 465 2-1 Example Compound 18 [(piq)₂Ir(acac)] 4.2 1850 0.6740.325 415 2-2 Example Compound 29 [(piq)₂Ir(acac)] 4.1 1900 0.672 0.327390 2-3 Example Compound 40 [(piq)₂Ir(acac)] 4.3 1740 0.673 0.335 4752-4 Example CBP [(piq)₂Ir(acac)] 7.5 1220 0.679 0.339 285 2

From the test results, it was identified that the red organic lightemitting devices of Examples 2-1 to 2-4 using the compounds representedby Compounds 7, 18, 29 and 40 prepared according to the presentdisclosure as a host material of the light emitting layer exhibitedsuperior performance in terms of current efficiency, driving voltage andlifespan compared to the red organic light emitting device of Example 2using existing CBP. Particularly, it was seen that the compounds havingcarbazole as a substituent were suitable for a red organic lightemitting device.

Example 3-1

A glass substrate on which indium tin oxide (ITO) was coated as a thinfilm to a thickness of 1,000 Å was placed in detergent-dissolveddistilled water and ultrasonic cleaned. Herein, a product of Fischer Co.was used as the detergent, and as the distilled water, distilled waterfiltered twice with a filter manufactured by Millipore Co. was used.After the ITO was cleaned for 30 minutes, ultrasonic cleaning wasrepeated twice using distilled water for 10 minutes. After the cleaningwith distilled water was finished, the substrate was ultrasonic cleanedwith solvents of isopropyl alcohol, acetone and methanol, then dried,and then transferred to a plasma cleaner. In addition, the substrate wascleaned for 5 minutes using oxygen plasma, and then transferred to avacuum depositor.

On the transparent ITO electrode prepared as above, a hole injectionlayer was formed by thermal vacuum depositing hexanitrilehexaazatriphenylene (HAT) of the following chemical formula to athickness of 500 Å.

A hole transfer layer was formed on the hole injection layer by vacuumdepositing the following compound4-4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å), a materialtransferring holes.

Subsequently, a light emitting layer was formed on the hole transferlayer to a film thickness of 300 Å by vacuum depositing BH and BD shownbelow in a weight ratio of 25:1.

An electron injection and transfer layer was formed on the lightemitting layer to a thickness of 300 Å by vacuum depositing the Compound1 prepared in Preparation Example 1 and the compound lithium quinolate(LiQ) in a weight ratio of 1:1. A cathode was formed on the electroninjection and transfer layer by depositing lithium fluoride (LiF) to athickness of 12 Å and aluminum to a thickness of 2,000 Å in consecutiveorder.

An organic light emitting device was manufactured by maintaining, in theabove-mentioned processes, the deposition rates of the organic materialsat 0.4 Å/sec to 0.7 Å/sec, the deposition rates of the lithium fluorideand the aluminum of the cathode at 0.3 Å/sec and 2 Å/sec, respectively,and the degree of vacuum during the deposition at 2×10⁷ torr to 5×10torr.

Example 3-2

An experiment was carried out in the same manner as in Example 3-1except that Compound 5 was used instead of Compound 1 as the electrontransfer layer.

Example 3-3

An experiment was carried out in the same manner as in Example 3-1except that Compound 8 was used instead of Compound 1 as the electrontransfer layer.

Example 3-4

An experiment was carried out in the same manner as in Example 3-1except that Compound 9 was used instead of Compound 1 as the electrontransfer layer.

Example 3-5

An experiment was carried out in the same manner as in Example 3-1except that Compound 12 was used instead of Compound 1 as the electrontransfer layer.

Example 3-6

An experiment was carried out in the same manner as in Example 3-1except that Compound 16 was used instead of Compound 1 as the electrontransfer layer.

Example 3-7

An experiment was carried out in the same manner as in Example 3-1except that Compound 19 was used instead of Compound 1 as the electrontransfer layer.

Example 3-8

An experiment was carried out in the same manner as in Example 3-1except that Compound 20 was used instead of Compound 1 as the electrontransfer layer.

Example 3-9

An experiment was carried out in the same manner as in Example 3-1except that Compound 23 was used instead of Compound 1 as the electrontransfer layer.

Example 3-10

An experiment was carried out in the same manner as in Example 3-1except that Compound 27 was used instead of Compound 1 as the electrontransfer layer.

Example 3-11

An experiment was carried out in the same manner as in Example 3-1except that Compound 30 was used instead of Compound 1 as the electrontransfer layer.

Example 3-12

An experiment was carried out in the same manner as in Example 3-1except that Compound 31 was used instead of Compound 1 as the electrontransfer layer.

Example 3-13

An experiment was carried out in the same manner as in Example 3-1except that Compound 34 was used instead of Compound 1 as the electrontransfer layer.

Example 3-14

An experiment was carried out in the same manner as in Example 3-1except that Compound 38 was used instead of Compound 1 as the electrontransfer layer.

Example 3-15

An experiment was carried out in the same manner as in Example 3-1except that Compound 41 was used instead of Compound 1 as the electrontransfer layer.

Example 3-16

An experiment was carried out in the same manner as in Example 3-1except that Compound 42 was used instead of Compound 1 as the electrontransfer layer.

Example 3

An experiment was carried out in the same manner as in Example 3-1except that the following Compound ET 1 was used instead of Compound 1as the electron transfer layer.

When a current was applied to the organic light emitting devicesmanufactured in Examples 3-1 to 3-16, and Example 3, results of Table 6were obtained.

TABLE 6 Compound (Electron Efficiency EL Transfer Voltage (cd/A@10 mA/Peak Category Layer) (V@10 mA/cm²) cm²) (nm) Example 3-1 Compound 1 6.2846.93 517 Example 3-2 Compound 5 6.36 45.24 516 Example 3-3 Compound 86.35 45.79 518 Example 3-4 Compound 9 6.29 46.15 517 Example 3-5Compound 12 6.38 45.31 515 Example 3-6 Compound 16 6.33 45.63 516Example 3-7 Compound 19 6.39 45.62 516 Example 3-8 Compound 20 6.3745.64 517 Example 3-9 Compound 23 6.24 46.68 518 Example 3- Compound 276.38 45.83 517 10 Example 3- Compound 30 6.36 45.24 516 11 Example 3-Compound 31 6.44 44.94 518 12 Example 3- Compound 34 6.35 45.22 517 13Example 3- Compound 38 6.33 45.75 515 14 Example 3- Compound 41 6.1547.16 516 15 Example 3- Compound 42 6.24 46.34 516 16 Example 3 ET 17.45 35.52 517

As seen from Table 6, it was identified that electron transfer andinjection abilities were excellent when comparing Examples 3-1 to 3-16,and Example 3. Particularly, it was seen that the compounds havingtriazine, benzimidazole or arylphosphine oxide as a substituent weresuitable as a material of the organic light emitting device.

Hereinbefore, preferred embodiments of the present disclosure (greenlight emitting layer, red light emitting layer, electron transfer layer)have been described, however, the present disclosure is not limitedthereto, and various modifications may be made within the scope of theclaims and the detailed descriptions, and the modifications are alsoincluded in the scope of the present disclosure.

The invention claimed is:
 1. A compound represented by the followingChemical Formula 1:

wherein, in Chemical Formula 1, L is a direct bond; a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group, HAr is a substituted or unsubstituted heterocyclicgroup; or a substituted or unsubstituted phosphine oxide group, R1 to R4are the same as or different from each other, and each independentlyhydrogen; deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; asubstituted or unsubstituted amine group; a substituted or unsubstitutedsilyl group; a substituted or unsubstituted boron group; a substitutedor unsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted aralkyl group; a substituted orunsubstituted aralkenyl group; a substituted or unsubstituted alkylarylgroup; a substituted or unsubstituted alkylamine group; a substituted orunsubstituted aralkylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted arylheteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group, or bond to an adjacentgroup to form a substituted or unsubstituted ring, a is an integer of 0to 7, b is an integer of 0 to 7, c is an integer of 0 to 5, d is aninteger of 0 to 4, n is an integer of 0 to 10, and when a, b, c, d and nare each 2 or greater, structures in the parentheses are the same as ordifferent from each other.
 2. The compound of claim 1, wherein ChemicalFormula 1 is represented by one of the following Chemical Formulae 2 to5:

wherein, in Chemical Formulae 2 to 5, definitions of substituents arethe same as in Chemical Formula
 1. 3. The compound of claim 1, whereinHAr is a substituted or unsubstituted pyridyl group; a substituted orunsubstituted pyrimidyl group; a substituted or unsubstituted triazinylgroup; a substituted or unsubstituted furan group; a substituted orunsubstituted thiophene group; a substituted or unsubstituted oxadiazolegroup; a substituted or unsubstituted thiadiazole group; a substitutedor unsubstituted phenanthroline group; a substituted or unsubstitutedquinolinyl group; a substituted or unsubstituted isoquinolinyl group; asubstituted or unsubstituted quinazoline group; a substituted orunsubstituted benzoxazole group; a substituted or unsubstitutedbenzothiazole group; a substituted or unsubstituted benzimidazole group;a substituted or unsubstituted phenoxazine group; a substituted orunsubstituted phenothiazine group; a substituted or unsubstituteddibenzofuran group; a substituted or unsubstituted dibenzothiophenegroup; a substituted or unsubstituted carbazole group; or a substitutedor unsubstituted diarylphosphine oxide group.
 4. The compound of claim1, wherein -(L)n-HAr is represented by the following structuralformulae:

wherein, in the structural formulae, Ar1 to Ar3 are the same as ordifferent from each other, and each independently a substituted orunsubstituted aryl group; a substituted or unsubstituted heterocyclicgroup; a substituted or unsubstituted arylamine group; a substituted orunsubstituted heteroarylamine group; or a substituted or unsubstitutedarylheteroarylamine group, L1 is a direct bond; a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group, and the structures are unsubstituted or substitutedwith one or more substituents selected from the group consisting ofdeuterium; a halogen group; a nitrile group; a nitro group; a hydroxylgroup; a carbonyl group; an ester group; an imide group; a substitutedor unsubstituted amine group; a phosphine oxide group; an alkoxy group;an aryloxy group; an alkylthioxy group; an arylthioxy group; analkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group;an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; anaralkyl group; an aralkenyl group; an alkylaryl group; an alkylaminegroup; an aralkylamine group; a heteroarylamine group; an arylaminegroup; an arylphosphine group; and a heterocyclic group.
 5. The compoundof claim 1, wherein L is a direct bond; or selected from among thefollowing structures:

wherein, in the structural formulae, A1 and A2 are the same as ordifferent from each other, and each independently hydrogen; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heterocyclic group, orbond to each other to form a substituted or unsubstituted ring, and thestructures are unsubstituted or substituted with one or moresubstituents selected from the group consisting of deuterium; a halogengroup; a nitrile group; a nitro group; a hydroxyl group; a carbonylgroup; an ester group; an imide group; an amine group; a phosphine oxidegroup; an alkoxy group; an aryloxy group; an alkylthioxy group; anarylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silylgroup; a boron group; an alkyl group; a cycloalkyl group; an alkenylgroup; an aryl group; an aralkyl group; an aralkenyl group; an alkylarylgroup; an alkylamine group; an aralkylamine group; a heteroarylaminegroup; an arylamine group; an arylphosphine group; and a heterocyclicgroup.
 6. The compound of claim 1, wherein the compound of ChemicalFormula 1 is any one selected from among the following structuralformulae:


7. An organic light emitting device comprising: a first electrode; asecond electrode provided opposite to the first electrode; and one ormore organic material layers provided between the first electrode andthe second electrode, wherein one or more layers of the organic materiallayers include the compound of claim
 1. 8. The organic light emittingdevice of claim 7, wherein the organic material layer includes a lightemitting layer, and the light emitting layer includes the compound. 9.The organic light emitting device of claim 8, wherein the light emittinglayer further includes a light emitting dopant.
 10. The organic lightemitting device of claim 7, wherein the organic material layer includesan electron injection layer, an electron transfer layer, or a layercarrying out electron transfer and electron injection at the same time,and the electron injection layer, the electron transfer layer, or thelayer carrying out electron transfer and electron injection at the sametime includes the compound.
 11. The organic light emitting device ofclaim 10, wherein the electron transfer layer further includes an n-typedopant.
 12. The organic light emitting device of claim 7, wherein theorganic material layer includes a hole injection layer, a hole transferlayer, a layer carrying out hole injection and transfer at the sametime, or an electron suppression layer, and the hole injection layer,the hole transfer layer, the layer carrying out hole injection andtransfer at the same time, or the electron suppression layer includesthe compound.
 13. The organic light emitting device of claim 7, whereinthe organic material layer includes a light emitting layer, and thelight emitting layer includes a compound represented by the followingChemical Formula 1-A:

wherein, in Chemical Formula 1-A, z1 is an integer of 1 or greater, andwhen z1 is an integer of 2 or greater, structures in the parentheses arethe same as or different from each other, Ar100 is a substituted orunsubstituted monovalent or higher benzofluorene group; a substituted orunsubstituted monovalent or higher fluoranthene group; a substituted orunsubstituted monovalent or higher pyrene group; or a substituted orunsubstituted monovalent or higher chrysene group, L100 is a directbond; a substituted or unsubstituted arylene group; or a substituted orunsubstituted heteroarylene group, and R100 and R101 are the same as ordifferent from each other, and each independently a substituted orunsubstituted aryl group; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted silyl group; a substituted or unsubstitutedarylalkyl group; or a substituted or unsubstituted heterocyclic group,or bond to each other to form a substituted or unsubstituted ring. 14.The organic light emitting device of claim 13, wherein z1 is 2, Ar100 isa divalent pyrene group, L100 is a direct bond, and R100 and R101 arethe same as or different from each other and each independently an arylgroup unsubstituted or substituted with an alkylgermanium group.
 15. Theorganic light emitting device of claim 7, wherein the organic materiallayer includes a light emitting layer, and the light emitting layerincludes a compound represented by the following Chemical Formula 1-B:

wherein, in Chemical Formula 1-B, Ar101 and Ar102 are the same as ordifferent from each other, and each independently a substituted orunsubstituted aryl group; or a substituted or unsubstituted heterocyclicgroup, L101 and L102 are the same as or different from each other, andeach independently a direct bond; a substituted or unsubstituted arylenegroup; or a substituted or unsubstituted heteroarylene group, R102 ishydrogen; deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; asubstituted or unsubstituted amine group; a substituted or unsubstitutedsilyl group; a substituted or unsubstituted boron group; a substitutedor unsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted aralkyl group; a substituted orunsubstituted aralkenyl group; a substituted or unsubstituted alkylarylgroup; a substituted or unsubstituted alkylamine group; a substituted orunsubstituted aralkylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted arylheteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group, z2 and z3 are the sameas or different from each other and each independently an integer of 1or 2, z4 is an integer of 0 to 8, and when z2 to z4 are 2 or greater,substituents in the parentheses are the same as or different from eachother, and m is an integer of 1 or greater, and when m is an integer of2 or greater, substituents in the parentheses are the same as ordifferent from each other.
 16. The organic light emitting device ofclaim 15, wherein Ar101 is a 2-naphthyl group, Ar102 is a phenyl group,L101 is a phenylene group, L102 is a direct bond, z2 is 1, R102 ishydrogen, and m is
 1. 17. The organic light emitting device of claim 13,wherein the light emitting layer includes a compound represented by thefollowing Chemical Formula 1-B:

wherein, in Chemical Formula 1-B, Ar101 and Ar102 are the same as ordifferent from each other, and each independently a substituted orunsubstituted aryl group; or a substituted or unsubstituted heterocyclicgroup, L101 and L102 are the same as or different from each other, andeach independently a direct bond; a substituted or unsubstituted arylenegroup; or a substituted or unsubstituted heteroarylene group, R102 ishydrogen; deuterium; a halogen group; a nitrile group; a nitro group; ahydroxyl group; a carbonyl group; an ester group; an imide group; asubstituted or unsubstituted amine group; a substituted or unsubstitutedsilyl group; a substituted or unsubstituted boron group; a substitutedor unsubstituted alkyl group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted alkoxy group; a substituted orunsubstituted aryloxy group; a substituted or unsubstituted alkylthioxygroup; a substituted or unsubstituted arylthioxy group; a substituted orunsubstituted alkylsulfoxy group; a substituted or unsubstitutedarylsulfoxy group; a substituted or unsubstituted alkenyl group; asubstituted or unsubstituted aralkyl group; a substituted orunsubstituted aralkenyl group; a substituted or unsubstituted alkylarylgroup; a substituted or unsubstituted alkylamine group; a substituted orunsubstituted aralkylamine group; a substituted or unsubstitutedheteroarylamine group; a substituted or unsubstituted arylamine group; asubstituted or unsubstituted arylheteroarylamine group; a substituted orunsubstituted arylphosphine group; a substituted or unsubstitutedphosphine oxide group; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heterocyclic group, z2 and z3 are the sameas or different from each other and each independently an integer of 1or 2, z4 is an integer of 0 to 8, and when z2 to z4 are 2 or greater,substituents in the parentheses are the same as or different from eachother, and m is an integer of 1 or greater, and when m is an integer of2 or greater, substituents in the parentheses are the same as ordifferent from each other.